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WO2007015260A3 - Ameliorations apportees a la synthese de l'hydroxyanisole butyle a partir de l'hydroquinone de butyle tertiaire - Google Patents

Ameliorations apportees a la synthese de l'hydroxyanisole butyle a partir de l'hydroquinone de butyle tertiaire Download PDF

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Publication number
WO2007015260A3
WO2007015260A3 PCT/IN2006/000132 IN2006000132W WO2007015260A3 WO 2007015260 A3 WO2007015260 A3 WO 2007015260A3 IN 2006000132 W IN2006000132 W IN 2006000132W WO 2007015260 A3 WO2007015260 A3 WO 2007015260A3
Authority
WO
WIPO (PCT)
Prior art keywords
bha
tertiary butyl
butylated hydroxyanisole
butyl hydroquinone
synthesis
Prior art date
Application number
PCT/IN2006/000132
Other languages
English (en)
Other versions
WO2007015260A2 (fr
Inventor
Mangesh Narayan Rajadhyaksha
Arun Kumar Sharma
Rajesh Shriram Gupta
Ajit Shripad Shirwaikar
Original Assignee
Camlin Fine Chemicals Ltd
Mangesh Narayan Rajadhyaksha
Arun Kumar Sharma
Rajesh Shriram Gupta
Ajit Shripad Shirwaikar
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Camlin Fine Chemicals Ltd, Mangesh Narayan Rajadhyaksha, Arun Kumar Sharma, Rajesh Shriram Gupta, Ajit Shripad Shirwaikar filed Critical Camlin Fine Chemicals Ltd
Priority to US11/918,838 priority Critical patent/US20090312582A1/en
Priority to CN200680022019XA priority patent/CN101583586B/zh
Priority to EP06809905A priority patent/EP1896390A4/fr
Publication of WO2007015260A2 publication Critical patent/WO2007015260A2/fr
Publication of WO2007015260A3 publication Critical patent/WO2007015260A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé amélioré destiné à la production de nouvelles formes physiques de l'hydroxyanisole butylé (BHA), consistant à faire réagir de l'hydroquinone de butyle tertiaire (TBHQ) dans une plage de température comprise entre 30 et 50 °C environ avec un léger excédent stoechiométrique de sulfate de diméthyle et d'hydroxyde de sodium, la quantité d'hydroxyde de sodium ajoutée étant supérieure sur le plan stoechiométrique à la quantité de sulfate de diméthyle ajoutée. Une majeure partie du BHA formé lors de cette réaction est récupérée sous une forme cristalline contenant 99 % environ et, en général, au moins 99,5 % environ de 3-t-butyle-4-hydroxyanisole (3 isomères), et 100 ppm ou moins de TBHQ. Le BHA restant dans la liqueur mère après cristallisation est récupéré par distillation et possède le même degré de pureté que le BHA cristallin. La forme cristalline se présente à la fois sous une forme basse densité et sous une forme haute densité et peut être transformée en formes comprimées, y compris en flocons, en comprimés et analogue.
PCT/IN2006/000132 2005-04-19 2006-04-13 Ameliorations apportees a la synthese de l'hydroxyanisole butyle a partir de l'hydroquinone de butyle tertiaire WO2007015260A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US11/918,838 US20090312582A1 (en) 2005-04-19 2006-04-13 Synthesis of butylated hydroxyanisole from tertiary butyl hydroquinone
CN200680022019XA CN101583586B (zh) 2005-04-19 2006-04-13 从邻叔丁基对苯二酚合成丁基羟基茴香醚的改进
EP06809905A EP1896390A4 (fr) 2005-04-19 2006-04-13 Ameliorations apportees a la synthese de l'hydroxyanisole butyle a partir de l'hydroquinone de butyle tertiaire

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN489MU2005 2005-04-19
IN489/MUM/2005 2005-04-19

Publications (2)

Publication Number Publication Date
WO2007015260A2 WO2007015260A2 (fr) 2007-02-08
WO2007015260A3 true WO2007015260A3 (fr) 2008-07-17

Family

ID=37709011

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2006/000132 WO2007015260A2 (fr) 2005-04-19 2006-04-13 Ameliorations apportees a la synthese de l'hydroxyanisole butyle a partir de l'hydroquinone de butyle tertiaire

Country Status (4)

Country Link
US (1) US20090312582A1 (fr)
EP (1) EP1896390A4 (fr)
CN (1) CN101583586B (fr)
WO (1) WO2007015260A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101704727B (zh) * 2009-10-29 2013-03-06 广东省食品工业研究所 一种从叔丁基羟基茴香醚生产过程中回收叔丁基对苯二酚的工艺
KR101367955B1 (ko) * 2011-11-10 2014-02-26 한국화학연구원 바이오디젤용 산화방지제 화합물로서 2―터셔리―부틸 하이드로퀴논의 제조방법.
CN108929202B (zh) * 2017-05-24 2021-02-19 中国人民解放军军事医学科学院生物医学分析中心 2-叔丁基-4-甲氧基苯酚制备新方法及其新晶型
CN108314609B (zh) * 2018-01-03 2021-04-13 兄弟科技股份有限公司 一种丁基羟基茴香醚的合成方法
CN113840819A (zh) * 2019-05-17 2021-12-24 罗地亚经营管理公司 纯化丁子香酚的方法及包含丁子香酚的新型组合物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2704746A (en) * 1950-08-16 1955-03-22 Universal Oil Prod Co Butylated hydroxyanisole flakes
US2722556A (en) * 1952-03-19 1955-11-01 Eastman Kodak Co Preparation of tertiary butyl hydroquinone
US2801268A (en) * 1957-07-30 Method of making z-tertiarybutyl-x-
GB1366441A (en) * 1971-06-23 1974-09-11 Eastman Kodak Co Preparation of antioxidant
US4898993A (en) * 1987-01-21 1990-02-06 Bromine Compounds Limited Process for preparing 2-tert-butyl-4-methoxyphenol

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776321A (en) 1957-01-01 Mgnoetherification of mono-tertiary-
US2887515A (en) 1959-05-19 Preparation of tertiary butyl-x-
GB763146A (en) * 1953-04-23 1956-12-05 Eastman Kodak Co Monoetherification of mono-tertiarybutyl hydroquinone using a hydrocarbon solvent
US4469897A (en) * 1980-11-13 1984-09-04 Anic S.P.A. Process for preparing monoalkylethers of hydroquinone and its derivatives
US4538002A (en) * 1984-09-10 1985-08-27 The Goodyear Tire & Rubber Company Process for the production of hydroxyanisole and alkylated hydroxyanisoles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2801268A (en) * 1957-07-30 Method of making z-tertiarybutyl-x-
US2704746A (en) * 1950-08-16 1955-03-22 Universal Oil Prod Co Butylated hydroxyanisole flakes
US2722556A (en) * 1952-03-19 1955-11-01 Eastman Kodak Co Preparation of tertiary butyl hydroquinone
GB1366441A (en) * 1971-06-23 1974-09-11 Eastman Kodak Co Preparation of antioxidant
US4898993A (en) * 1987-01-21 1990-02-06 Bromine Compounds Limited Process for preparing 2-tert-butyl-4-methoxyphenol

Also Published As

Publication number Publication date
CN101583586B (zh) 2013-05-08
US20090312582A1 (en) 2009-12-17
EP1896390A2 (fr) 2008-03-12
WO2007015260A2 (fr) 2007-02-08
CN101583586A (zh) 2009-11-18
EP1896390A4 (fr) 2010-05-19

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